Benzo(B)Thiophene-2-Boronic Acid → HCID 86686452, compound

HRID 2176814Notes

Reaction equation

HRID 2176814 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([S:21]([CH3:23])=[O:22])=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH:16]([CH2:18][CH2:19][CH3:20])[CH3:17])[CH:11]=[CH:10]2)(=O)=O.[S:26]1[C:30](B(O)O)=[CH:29][C:28]2[CH:34]=[CH:35][CH:36]=[CH:37][C:27]1=2.C([O-])([O-])=O.[K+].[K+]>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>[S:26]1[C:30]([C:7]2[C:8]([S:21]([CH3:23])=[O:22])=[C:9]3[C:13](=[CH:14][CH:15]=2)[N:12]([CH:16]([CH2:18][CH2:19][CH3:20])[CH3:17])[CH:11]=[CH:10]3)=[CH:29][C:28]2[CH:34]=[CH:35][CH:36]=[CH:37][C:27]1=2

Participants

6

Reactant 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 11430Potassium CarbonateHCID 86686450HCID 86686450, compound

Product 1

HCID 86686452HCID 86686452, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

To a deaerated solution of 4-(methylsulfinyl)-1-(pentan-2-yl)-1H-indol-5-yltrifluoromethanesulfonate 17) (0.40 g, 1.0 mmol) and benzo[b]thiophen-2-ylboronic acid (18) (0.35 g, 2.0 mmol), and Pd(PPh3)4 (60 mg, 0.05 mmol) in toluene (10 mL) was added aqueous K2CO3 (2M, 6.0 mL). The mixture was heated at 90° C. for 4 h. Toluene (20 mL) was added and the organic phase was washed with water (20 mL) and then concentrated to dryness in vacuo. The residual was purified by silica gel column chromatography (2:1 hexanes/ethyl acetate) to give 5-(benzo[b]thiophen-2-yl)-4-(methylsulfinyl)-1-(pentan-2-yl)-1H-indole (19) (0.26 g, 68%) as a yellow oil. 1H NMR (500 MHz, CD2Cl2): δ 7.88 (d, J=8.0, 1H), 7.85 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.40 (m, 4H), 7.35 (d, J=3.5, 1H), 7.2 9s, 1H), 4.62 (m, 1H), 3.00 (d, 3H), 1.88 (m, 2H), 1.57 (m, 3H), 1.24 (m, 2H), 0.93 (m, 3H). Mass (ESI, M+H): 382.7. See also Im, G-Y. J., et al., J. Am. Chem. Soc., 132:17933 (2010).

Workup

  1. washthe organic phase was washed with water (20 mL)
  2. concentrationconcentrated to dryness in vacuo
  3. customThe residual was purified by silica gel column chromatography (2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-ba4e995e10a247fabc352a9dc278ee31
Source dataset
uspto-grants-2015_06
Patent number
US09067886B2

Reaction notes

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