Dimethylformamide → HCID 44469658, compound

HRID 2382945Notes

Reaction equation

Br[C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7](COC)[C:8]([C:10]2[C:11]3[CH:12]=[N:13][N:14]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:15]=3[CH:16]=[CH:17][CH:18]=2)=[O:9])=[C:4]([Cl:31])[CH:3]=1.[CH3:32][N:33](C=O)C>[Cl-].[NH4+].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].[C-]#N.[C-]#N.[Zn+2].[Zn]>[Cl:31][C:4]1[CH:3]=[C:2]([C:32]#[N:33])[CH:30]=[CH:29][C:5]=1[CH2:6][NH:7][C:8]([C:10]1[C:11]2[CH:12]=[N:13][N:14]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:15]=2[CH:16]=[CH:17][CH:18]=1)=[O:9]

Participants

Conditions

Temperature: 120 °C

Procedure

In a sealed tube, 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (4-bromo-2-chloro-benzyl)-methoxymethyl-amide (0.30 g, 0.65 mmol), Pd2(dba)3 (40.0 mg, 0.440 mmol), dppf (44 mg, 0.079 mmol), Zn(CN)2 (77 mg, 0.66 mmol), and Zn (10.5 mg, 0.160 mmol) were dissolved in anhydrous DMF (3 mL). The mixture was warmed at 120° C. for 3 hours. The mixture cooled to room temperature, and diluted with saturated aqueous ammonium chloride (20 mL), extracted with ethyl acetate (20 mL), washed with brine (30 mL), and dried over sodium sulfate. The crude was purified by silica gel chromatography eluting with a gradient of 0-70% ethyl acetate in hexanes to afford the title compound as a white powder.

Workup

temperatureThe mixture cooled to room temperature
extractionextracted with ethyl acetate (20 mL)
washwashed with brine (30 mL)
dry with materialdried over sodium sulfate
customThe crude was purified by silica gel chromatography
washeluting with a gradient of 0-70% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-d8be9d3799274142b871545bf70d13b2
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263597B2

Reaction notes

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