Sodium Bicarbonate → HCID 71765497, compound

HRID 2272961Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:17])[C:11]3[N:12]([CH:14]=[CH:15][CH:16]=3)[CH:13]=2)=[CH:4][CH:3]=1.[CH3:18][N:19]1[CH:23]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:21]=[N:20]1.C(=O)([O-])O.[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:18][N:19]1[CH:23]=[C:22]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:9][C:10](=[O:17])[C:11]4[N:12]([CH:14]=[CH:15][CH:16]=4)[CH:13]=3)=[CH:4][CH:3]=2)[CH:21]=[N:20]1

Participants

Conditions

Temperature: 40 °C

Procedure

Under nitrogen, a suspension of 141 mg (0.486 mmol) 3-(4-bromo-phenyl)-2H-pyrrolo[1,2-a]pyrazin-1-one, 111 mg (0.534 mmol) 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole and 49 mg (0.58 mmol) sodium hydrogen carbonate in 1 ml DMF and 0.5 ml water is heated to 40° C. Then 6.8 mg (0.010 mmol) bis(triphenylphosphine)-palladium(II)-chloride is added. The reaction mixture is heated to 80° C. and stirred at this temperature for 20 hours. The reaction mixture is cooled to room temperature and excess water is added. The resulting precipitate is filtered off and washed with water. The residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent to give 3-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]-2H-pyrrolo[1,2-a]pyrazin-1-one as light yellow crystals; HPLC/MS 2.09 min (B), [M+H] 291;

Workup

temperatureThe reaction mixture is heated to 80° C.
temperatureThe reaction mixture is cooled to room temperature
filtrationThe resulting precipitate is filtered off
washwashed with water
customThe residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent

Sources & evidence

ORD record: ord-8d973d385e4644fa9eb6b3d4e9c99077
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120805B2

Reaction notes

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