Hydrochloric Acid → 5-bromo-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

HRID 661990노트

반응식

HRID 661990 반응식
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7](C(OCC)=O)[CH2:8][C:9]=1[NH:10]2.[CH3:23][Li].Cl.[CH2:26]1[CH2:30][O:29]CC1>>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([NH2:16])=[O:17])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([C:30]([OH:29])([CH3:26])[CH3:23])[CH2:8][C:9]=1[NH:10]2

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 59375013ethyl 5-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate2회HCID 178418348HCID 178418348, 화합물

생성물 1

HCID 593750225-bromo-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide수율 89%

실험 절차

A solution of ethyl 5-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate (Intermediate 46-1, 2 g, 5.48 mmol) in THF (100 mL) cooled in an ice bath was treated with methyllithium (1.6 M in diethyl ether, 17.11 mL, 27.4 mmol). After 1 h, the mixture was treated slowly with a mixture of 1 M hydrochloric acid (20 mL) and ice (20 g). The organic layer was separated, and the aqueous layer was extracted twice with DCM. The combined organic phases were washed with water and brine, dried and concentrated. The residue was triturated with DCM to provide 5-bromo-2-(2-hydroxypropan-2-yl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a light yellow solid (1.72 g, 89%). 1H NMR (400 MHz, methanol-d4) δ 7.38 (1H, d, J=8.14 Hz), 7.16 (1H, d, J=8.14 Hz), 3.37-3.45 (1H, m), 2.90-2.97 (1H, m), 2.79-2.89 (1H, m), 2.54-2.64 (1H, m), 2.20-2.28 (1H, m), 1.80-1.90 (1H, m, J=11.94, 11.94, 4.95, 2.20 Hz), 1.41-1.53 (1H, m, J=12.43, 12.43, 12.32, 5.28 Hz), 1.30 (6H, s). Mass spectrum m/z 351, 353 (M+H)+.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted twice with DCM
  3. washThe combined organic phases were washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was triturated with DCM

출처 및 근거

ORD 기록
ord-a6bdf52f440a4fedb1f85f666f126a68
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084620B2

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