Sodium borohydride → 3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

HRID 2193645Notes

Reaction equation

[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:19])[CH:16]=[CH:17][N:18]=3)[S:13][C:6]=12.[BH4-].[Na+]>CO.C1COCC1>[F:1][C:2]1[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:19])[CH:16]=[CH:17][N:18]=3)[S:13][C:6]=12

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the nitro compound 8 (1.50 g, 4.05 mmol) and NiCl2.6H2O (2.02 g, 8.52 mmol) in MeOH/THF (45 mL/68 mL) at 0° C. was added NaBH4 (0.618 g, 16.3 mmol) portion wise with vigorous stirring. The reaction mixture was stirred for 30 minutes at 0° C. and concentrated under reduced pressure. The resultant black residue was suspended in 1M HCl (10 mL) and the mixture was basified (pH˜11) with cone. NH4OH. The cloudy suspension was filtered; the solid residue was separated, washed with water and dried under reduced pressure to afford the title compound 9 as a brown solid (0.73 g, 52% yield), which was used in the next step without further purification. MS (m/z): 341.1 (M+H).

Workup

concentrationconcentrated under reduced pressure
filtrationThe cloudy suspension was filtered
customthe solid residue was separated
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-c06236a1dc9f459dafa730fa1d0e73bc
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329726B2

Reaction notes

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