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Hydrochloric Acid → {3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol

HRID 886555
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HRID 886555 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]([C:26]4[C:31]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:29]=[CH:28][N:27]=4)[OH:25])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[N:11](S(C2C=CC(C)=CC=2)(=O)=O)[CH:10]=1.Cl>C(O)C.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]([C:26]4[C:31]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:29]=[CH:28][N:27]=4)[OH:25])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[NH:11][CH:10]=1
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참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 59824986{3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol

생성물 1

HCID 59824848{3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol수율 49%

시약·촉매·용매 2

HCID 702Ethanol용매
HCID 14798
Sodium Hydroxide
용매

실험 절차

390 mg (0.62 mmol) of {3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol was dissolved in ethanol under gentle warming. The resulting solution was diluted with 2 M aqueous sodium hydroxide (16-30% v/v) and the resulting mixture was left at room temperature for 16 h. The pH was adjusted to 8 by addition of concentrated aqueous hydrochloric acid and the resulting solution was extracted three times with chloroform. The combined organic phases were dried over sodium sulfate and evaporated to afford 144 mg (0.30 mmol, 49%) of {3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-(3-trifluoromethyl-pyridin-2-yl)-methanol as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 11.93 (d, 1H), 8.86 (d, 1H), 8.49 (d, 1H), 8.20 (dd, 1H), 8.11 (d, 1H), 7.75 (s, br., 1H), 7.73 (d, 1H), 7.58 (d(m), 1H), 7.56 (d, 1H), 7.54 (dd, 1H), 7.40 (t, 1H), 7.32-7.29 (m, 2H), 7.15 (dd, 1H), 7.05 (dd, 1H), 6.23 (d, 1H), 6.09 (d, 1H), 3.82 (s, 3H); MS: m/z 476.1 (M+H+).

후처리

  1. extractionthe resulting solution was extracted three times with chloroform
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated

출처 및 근거

ORD 기록
ord-cb7d5a64c36e4021b36071ba7df6a2c0
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242280B2

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