Methanol → HCID 59375119, compound

HRID 661999Notes

Reaction equation

HRID 661999 reaction equation
[F:1][C:2]1[C:7]([O:8]C)=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:22]2[C:21]3[C:16](=[CH:17][C:18]([C:23]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)=[O:24])=[CH:19][CH:20]=3)[NH:15][C:14]=2[C:13]([C:32]([NH2:34])=[O:33])=[CH:12][CH:11]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:22]2[C:21]3[C:16](=[CH:17][C:18]([C:23]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)=[O:24])=[CH:19][CH:20]=3)[NH:15][C:14]=2[C:13]([C:32]([NH2:34])=[O:33])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 66606357HCID 66606357, compound

Product 1

HCID 59375119HCID 59375119, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-fluoro-3-methoxyphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide (Example 3-137, 3.6 g, 7.82 mmol) in DCM (42 mL) was stirred at 0° C. and treated with boron tribromide (1 M in DCM, 94 mL, 94 mmol) and the mixture was stirred at rt overnight. The mixture was cooled again to 0° C. and treated slowly with methanol. The mixture was concentrated and purified by column chromatography on neutral alumina (eluting with 90:10 EtOAc-methanol) to provide 4-(2-fluoro-3-hydroxyphenyl)-7-(4-methylpiperazine-1-carbonyl)-9H-carbazole-1-carboxamide as a light colored solid (2.0 g, 57%). 1H NMR (400 MHz, DMSO-d6) δ 11.75 (s, 1H), 10.08 (s, 1H), 8.25 (br. s., 1H), 8.05 (d, J=7.6 Hz, 1H), 7.81 (s, 1H), 7.59 (br. s., 1H), 7.17 (m, 3H), 7.11 (d, J=7.6 Hz, 1H), 6.99 (dd, J=8.0, 1.2 Hz, 1H), 6.91 (t, J=7.2 Hz, 1H), 3.51 (br. s., 2H), 3.34 (m, 5H), 2.34 (br. s., 4H). Mass spectrum m/z 447.0 (M+H)+.

Workup

  1. temperatureThe mixture was cooled again to 0° C.
  2. concentrationThe mixture was concentrated
  3. custompurified by column chromatography on neutral alumina (eluting with 90:10 EtOAc-methanol)

Sources & evidence

ORD record
ord-d095c9c303b541d4a1b030c9a3045010
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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