Potassium Carbonate → HCID 69299887, compound

HRID 2054591Notes

Reaction equation

HRID 2054591 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@@H:4]1[CH2:8][CH:7]([S:9][C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)[CH2:6][N:5]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[CH:25]1[C:33]2[C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[O:30][C:29]=2[C:28]([C:38]2[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=2)=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.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>[CH3:1][O:2][C:3](=[O:24])[C@@H:4]1[CH2:8][CH:7]([S:9][C:10]2[CH:15]=[CH:14][C:13]([C:41]3[CH:42]=[CH:43][C:38]([C:28]4[C:29]5[O:30][C:31]6[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=6[C:33]=5[CH:25]=[CH:26][CH:27]=4)=[CH:39][CH:40]=3)=[CH:12][CH:11]=2)[CH2:6][N:5]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 59655966(4-(Dibenzo[b,d]furan-4-yl)phenyl)boronic acidHCID 69298229HCID 69298229, compound

Product 1

HCID 69299887HCID 69299887, compoundYield 73%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4′-bromophenylsulfanyl)-N-tert-butoxycarbonyl-proline methyl ester (416 mg, 1 mmol), (4-Dibenzofuran-4-yl-phenyl)boronic acid (302 mg, 1.05 mmol), Pd(PPh3)4 (52 mg, 5% mol) in toluene (10 mL) and ethanol (2.5 mL) was heated until the solution became clear and subsequently treated with 2 M K2CO3 (1.5 mL). The reaction mixture was heated to reflux for 2 h, cooled to room temperature, diluted with ethyl acetate (100 mL). The organic layer was washed successively with 2% aq HCl and sat. aq NaCl, dried over MgSO4 and concentrated. Purification by flash column chromatography (2-10% ethyl acetate in heptane) to give 4-(4′-dibenzofuran-4-yl-bipheny-4-ylsulfanyl)-N-tert-butoxycarbonyl-proline methyl ester (410 mg, 73%). 1H NMR (CDCl3), δ 8.01 (m, 3H), 7.95 (d, J=6 Hz, 1H), 7.73 (d, J=7 Hz, 2H), 7.62 (m, 4H), 7.41 (m 5H), 4.37-4.28 (m, 1H), 4.01 (m, 1H), 3.76 (s, 3H), 3.69 (m, 1H), 3.42 (m, 1H), 2.67 (m, 1H), 2.07 (m, 1H), 1.44 (s, 9H). LCMS 580 (M++1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. washThe organic layer was washed successively with 2% aq HCl and sat. aq NaCl
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (2-10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b03ec9b8585b4b24a9bffd6064b527a0
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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