Water → HCID 10271479, compound

HRID 1297100Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]([CH3:23])[C:11](=[O:24])[CH2:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>CN(C=O)C>[C:2]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[C:14]3[CH:15]=[C:16]([O:21][CH3:22])[C:17]([O:19][CH3:20])=[CH:18][C:13]=3[N:12]([CH3:23])[C:11](=[O:24])[CH2:10][N:9]=2)[CH:3]=1

Participants

Conditions

Temperature: 115 °C

Procedure

Heat at 115° C. for 12 hours under an inert atmosphere a mixture of 100 mg (0.26 mmol) of 5-(3-bromophenyl)-7,8-dimethoxy-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one IIax, 38 mg (0.31 mmol) of benzene boronic acid, 63 mg (0.30 mmol) of K3PO4, 9 mg (0.020 mmol) of tetrakis(triphenylphosphine)Pd(0) in 1 ml of DMF. Allow to cool to room temperature. Add 80 ml of H2O and extract three times with 50 ml of Et2O. Dry the organic fractions on Na2SO4. Purify by chromatography (AcOEt 1/hexane 1). Recrystallize in EtOH. One obtains 13 mg of the abovenamed powder as colorless crystals. Yield: 13%. M: 127° C. 1H-NMR (CDCl3, 200 MHz): d 3.42 (s, 3H, NCH3), 3.77 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 4.34 (AB system, ?d=1.00, JAB=10.5, 2H, CH2), 6.78 (s, 1H Ar), 6.80 (s, 1H Ar), 7.39–7.90 (m, 9H Ar).

Workup

temperatureto cool to room temperature
extractionextract three times with 50 ml of Et2O
customDry the organic fractions on Na2SO4
customPurify by chromatography (AcOEt 1/hexane 1)
customRecrystallize in EtOH

Sources & evidence

ORD record: ord-4045f22068834c3ca62a6015a0db7940
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07250410B2

Reaction notes

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