Water → HCID 59699882, 화합물

HRID 901392노트

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HRID 901392 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:10](I)=[CH:9][N:8]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:5]2=[N:6][CH:7]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.ClCCl.O>C(#N)C.C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[O:23][CH3:22])=[CH:9][N:8]([Si:12]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[CH:13]([CH3:15])[CH3:14])[C:5]2=[N:6][CH:7]=1

참가 물질

8

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HCID 962WaterHCID 6344DichloromethaneHCID 27339582-Methoxyphenylboronic acidHCID 242292315-Bromo-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 59699882HCID 59699882, 화합물수율 73%

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6342Acetonitrile용매HCID 516892Sodium Bicarbonate용매

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온도
65 °C

실험 절차

1.01 g (2.10 mmol) of 5-bromo-3-iodo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine, 336 mg of 2-methoxyphenylboronic acid, and 75 mg of (1,1′-bis(diphenyl-phosphino)ferrocene)palladium(II)-dichloride dichloromethane adduct were placed in a Smith® vial and dissolved in a mixture of 15 ml of acetonitrile, 5 ml of toluene, and 7 ml of a saturated aqueous solution of sodium bicarbonate. The mixture was heated to 65° C. for 4 h and then cooled to room temperature. The crude was distributed between dichloromethane and water and the organic phase was dried over sodium sulfate and evaporated. The crude was then purified by flash chromatorgraphy on silica gel using a gradient of ethyl acetate in hexanes to afford 708 mg (1.53 mmol, 73%) of 5-bromo-3-(2-methoxy-phenyl)-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine as a yellow oil (containing about 20% of residual starting material as an inseparable mixture). 1H-NMR (d6-DMSO): δ8.33 (d, J=2.4 Hz, 1H), 8.15 (d, J=2.0 Hz, 1H), 7.76 (s, 1H), 7.55 (dd, J=1.3 Hz, 7.3 Hz, 1H), 7.33 (ddd, J=1.9 Hz, 7.3 Hz, 1H), 7.15 (dd, J=1.0 Hz, 8.3 Hz 1H), 7.06 (dt, J=1.0 Hz, 7.3 Hz, 1H), 3.82 (s, 3H), 1.88 (m, 3H), 1.10 (d, 18H).

후처리

  1. temperaturecooled to room temperature
  2. dry with materialthe organic phase was dried over sodium sulfate
  3. customevaporated
  4. customThe crude was then purified by flash chromatorgraphy on silica gel using a gradient of ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-3435e576e1cb41ef809b7e35e3f458e3
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361763B2

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