Water → HCID 90092470, compound

HRID 1774589Notes

Reaction equation

[BH4-].[Na+].[Br:3][C:4]1[C:8]([C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:18]=2)=[C:7]([C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21])[N:6]([CH3:25])[N:5]=1.O>O1CCCC1>[Br:3][C:4]1[C:8]([C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][CH2:15][CH2:14][C:13]=3[CH:18]=2)=[C:7]([CH:19]([OH:24])[C:20]([O:22][CH3:23])=[O:21])[N:6]([CH3:25])[N:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, sodium borohydride (36 mg, 0.95 mmol) was added portionwise to a solution of methyl 2-[3-bromo-4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-1H-pyrazol-5-yl]-2-oxoacetate (11g) (300 mg, 0.79 mmol) in anhydrous tetrahydrofuran (8 mL) at 0° C. After 30 minutes stirring at 0° C., water was added (5 mL) and the mixture was concentrated in vacuo. The crude was dissolved in ethyl acetate (10 mL) then successively washed with water (10 mL), and brine (10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (dichloromethane/ethyl acetate 80/20) to provide methyl 2-[3-bromo-4-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-1H-pyrazol-5-yl]-2-hydroxyacetate (11h) (204 mg, 0.54 mmol, 68%).

Workup

concentrationthe mixture was concentrated in vacuo
dissolutionThe crude was dissolved in ethyl acetate (10 mL)
washthen successively washed with water (10 mL), and brine (10 mL)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by preparative TLC (dichloromethane/ethyl acetate 80/20)

Sources & evidence

ORD record: ord-e101d26326f848659e4b0d6a2af4d647
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260395B2

Reaction notes

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