Sodium Hydroxide → HCID 86629453, compound

HRID 599296Notes

Reaction equation

[C:1]([NH:5][C:6]1[C:11]([CH:12]=O)=[CH:10][N:9]=[C:8]([Cl:14])[CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>CC(O)=O>[C:1]([NH:5][C:6]1[C:11]([CH2:12][NH:20][C:19]2[CH:21]=[CH:22][C:16]([F:15])=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[CH:10][N:9]=[C:8]([Cl:14])[CH:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(tert-butylamino)-6-chloronicotinaldehyde (4.0 g, 18.9 mmol), 4-fluoro-3-nitroaniline (2.9 g, 18.9 mmol) and NaBH(OAc)3 (7.1 g, 37.8 mmol) in CH3COOH (80 mL) was heated to 80° C. for 10 h. The reaction was concentrated under reduced pressure to give a sticky solid, which was suspended in ice water. The mixture was neutralized (pH 7) with 2N aqueous NaOH solution and was extracted with EtOAc. The extracts were washed with brine, dried Na2SO4) and concentrated in vacuo. Purification of the residue by chromatography provided N-tert-butyl-2-chloro-5-((4-fluoro-3-nitrophenylamino)methyl)pyridin-4-amine (4.3 g, 65% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.87 (s, 1 H), 7.32 (m, 1 H), 7.27 (m, 1 H), 7.04 (m, 1 H), 6.68 (s, 1 H), 6.52 (m, 1 H), 5.46 (s, 1 H), 4.17 (d, J=4.8 Hz, 2 H), 1.36 (s, 9 H).

Workup

concentrationThe reaction was concentrated under reduced pressure
customto give a sticky solid, which
extractionwas extracted with EtOAc
washThe extracts were washed with brine, dried Na2SO4) and
concentrationconcentrated in vacuo
customPurification of the residue by chromatography

Sources & evidence

ORD record: ord-7f3f0e51df134a5ebea7cdfbff0ebf68
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897762B2

Reaction notes

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