Sodium Bicarbonate → (6-chloro-pyrimidin-4-yl)-(1,7-dimethyl-1H-indazol-5-yl)-methanone

HRID 469362Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([CH3:12])[N:6]=[CH:5]2.C([Li])CCC.CON(C)[C:21]([C:23]1[CH:28]=[C:27]([Cl:29])[N:26]=[CH:25][N:24]=1)=[O:22].C(=O)([O-])O.[Na+]>C1COCC1>[Cl:29][C:27]1[N:26]=[CH:25][N:24]=[C:23]([C:21]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([CH3:11])[CH:10]=2)[N:7]([CH3:12])[N:6]=[CH:5]3)=[O:22])[CH:28]=1

Participants

Conditions

Temperature: -75 °C

Procedure

Under an argon atmosphere 0.450 g (2.00 mmol) 5-bromo-1,7-dimethyl-1H-indazole in 25 mL THF were cooled to −75° C., combined with 1.40 mL (2.24 mmol) of a 1.6 molar n-butyllithium solution and stirred for 1 h at −75° C. Then 0.480 g (2.14 mmol) 6-chloro-pyrimidine-4-carboxylic acid methoxy-methyl-amide were added dropwise. The mixture was brought to 0° C. and stirred for a further hour. Then saturated sodium hydrogen carbonate solution was stirred in, the mixture was extracted with EtOAc, the organic phase was dried and evaporated down i. vac. The residue was triturated with DIPE, suction filtered and dried. The precipitate was purified by flash chromatography (Alox).

Workup

customwas brought to 0° C.
stirringstirred for a further hour
extractionwas extracted with EtOAc
customthe organic phase was dried
customevaporated down i
customThe residue was triturated with DIPE, suction
filtrationfiltered
customdried
customThe precipitate was purified by flash chromatography (Alox)

Sources & evidence

ORD record: ord-c497278f1e9545689718fc3bd337f193
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629137B2

Reaction notes

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