HCID 10962863, compound → HCID 10962863, compound

HRID 1173068Notes

Reaction equation

HRID 1173068 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[C:10]([Sn:22]([CH2:31][CH2:32][CH2:33][CH3:34])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:36]1[O:37][C:38]([C:51]([CH3:59])([CH3:58])[O:52][SiH2:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[CH:39][C:40](=[O:50])[C:41]=1[O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][CH:18]=[C:19]([CH3:20])[CH3:21])[C:10]([Sn:22]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2].[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])[C:10]([C:36]2[O:37][C:38]([C:51]([CH3:59])([CH3:58])[O:52][SiH2:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[CH:39][C:40](=[O:50])[C:41]=2[O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 10962863HCID 10962863, compoundHCID 131728523HCID 131728523, compound

Product 2

HCID 10962863HCID 10962863, compoundHCID 131728522HCID 131728522, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

7-(3-Methyl-but-2-enyl)-3-tributylstannanyl-indole-1-carboxylic acid tert-butyl ester (203) was prepared according to the procedure developed by our group.23 Stannane 203 (1.146 g, 1.995 mmol) and 2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-pyran-4-one (600 mg, 1.33 mmol) were dissolved in toluene (10 mL). Tetrakis(triphenylphosphine)palladium (77 mg, 0.067 mmol) was added. Argon was bubbled through the resulting solution for 15 min to remove oxygen. The mixture was heated to 90° C. and stirred for 20 h. The mixture was cooled to room temperature, diluted with ether and washed with saturated aqueous KF solution several times. The organic layer was dried over Na2SO4 then solvent removed under vacuum. After flash column chromatography, the desired product was obtained as a light yellow oil (532 mg, 61%). 1H NMR (CDCl3): δ 0.15 (6H, s), 0.29 (6H, s), 0.92 (9H, s), 0.96 (9H, s), 1.65 (9H, s), 1.70 (3H, s), 3.77 (2H, d, J=6.6 Hz), 4.60 (2H, s), 5.24 (1H, m), 6.48 (1H, s), 7.2-7.3 (2H, m), 7.86 (1H, m), 8.24 (1H, s). 13C NMR (CDCl3): δ −5.2, −2.8, 18.2, 18.5, 19.2, 22.5, 26.0, 26.5, 28.2, 31.6, 33.6, 61.8, 84.7, 111.0, 119.5, 123.0, 124.1, 126.3, 127.2, 129.2, 129.6, 130.9, 133.4, 134.2, 137.6, 141.5, 149.2, 149.6, 165.0, 175.3. IR (KBr): 3150, 2895, 1576, 1269, 1151 cm−1. HRMS (EI): m/z Caled. for C36H55NO6Si2 [M+] 653.3568, found 653.3577.

Workup

  1. customArgon was bubbled through the resulting solution for 15 min
  2. customto remove oxygen
  3. temperatureThe mixture was cooled to room temperature
  4. additiondiluted with ether
  5. washwashed with saturated aqueous KF solution several times
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customsolvent removed under vacuum

Sources & evidence

ORD record
ord-eaec63576f064136be0c17f2737d51ed
Source dataset
uspto-grants-2010_11
Patent number
US07834050B2

Reaction notes

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