Water → HCID 117601900, compound

HRID 1773703Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9](I)[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:18])[O:4][N:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26](B(O)O)=[CH2:27])=[CH:22][CH:21]=1.N12CCCN=C1CCCCC2.O>CN1CCCC1=O>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:26]([C:23]3[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=3)=[CH2:27])[C:10]3[NH:14][C:13](=[O:15])[NH:12][C:11]=3[CH:16]=2)=[C:5]([CH3:18])[O:4][N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

6-(3,5-Dimethylisoxazol-4-yl)-4-iodo-1H-benzo[d]imidazol-2(3H)-one (100 mg, 0.28 mmol), 1-(4-Fluorophenyl)vinylboronic acid, pinacol ester (209.59 mg, 0.84 mmol), PEPPSI″-IPr catalyst (19.19 mg, 0.03 mmol), 1,8-Diazabicyclo[5.4.0]undec-7-ene solution (0.25 ml, 1.69 mmol) were mixed in 1-Methyl-2-pyrrolidinone (6 ml) and Water (3 ml) in sealed in a microwave vial and heated to 110° C. for 30 minutes in a microwave reactor. The reaction mixture was then cooled and partitioned between water and ethyl acetate. The organic layer was washed with water then brine and dried over sodium sulfate. Purification on silica gel (Hexane/EtOAc) followed by preparative HPLC afforded 6-(3,5-dimethylisoxazol-4-yl)-4-(1-(4-fluorophenyl)vinyl)-1H-benzo[d]imidazol-2(3H)-one.

Workup

temperatureThe reaction mixture was then cooled
custompartitioned between water and ethyl acetate
washThe organic layer was washed with water
dry with materialbrine and dried over sodium sulfate
customPurification on silica gel (Hexane/EtOAc)

Sources & evidence

ORD record: ord-fd46d484526645fc83d75980860c6196
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255089B2

Reaction notes

Loading…