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

HRID 1811170ノート

反応式

HRID 1811170 の反応式
[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

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 59375013ethyl 5-bromo-8-carbamoyl-2,3,4,9-tetrahydro-1H-carbazole-2-carboxylate2 回HCID 178418348HCID 178418348、化合物

生成物 1

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

実験手順

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) δ7.38 (1 H, d, J=8.14 Hz), 7.16 (1 H, d, J=8.14 Hz), 3.37-3.45 (1 H, m), 2.90-2.97 (1 H, m), 2.79-2.89 (1 H, m), 2.54-2.64 (1 H, m), 2.20-2.28 (1 H, m), 1.80-1.90 (1 H, m, J=11.94, 11.94, 4.95, 2.20 Hz), 1.41-1.53 (1 H, m, J=12.43, 12.43, 12.32, 5.28 Hz), 1.30 (6 H, s). Mass spectrum m/z 351, 353 (M+H)+.

後処理

  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

出典と根拠

ORDレコード
ord-aa3532587f9d43519e57e190626d42bf
出典データセット
uspto-grants-2013_01
特許番号
US08362065B2

反応ノート

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