2-(Dimethylamino)ethanol → (E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide

HRID 1256093Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:22][C:23](=[O:28])[C:24]([F:27])([F:26])[F:25])[CH:5]=[CH:6][C:7]=1[S:8](=[O:21])(=[O:20])[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:17][O:16][B:15]([OH:18])[C:14]=2[CH:19]=1.C([Sn](CCCC)(CCCC)/[CH:34]=[CH:35]/[O:36][CH2:37][CH3:38])CCC.CN(CCO)C>CN1C(=O)CCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:37]([O:36]/[CH:35]=[CH:34]/[C:2]1[CH:3]=[C:4]([NH:22][C:23](=[O:28])[C:24]([F:26])([F:27])[F:25])[CH:5]=[CH:6][C:7]=1[S:8](=[O:20])(=[O:21])[NH:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:17][O:16][B:15]([OH:18])[C:14]=2[CH:19]=1)[CH3:38]

Participants

Conditions

Temperature: 100 °C

Procedure

The mix of N-(3-bromo-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide (87 mg, 0.182 mmol), (E)-tributyl(2-ethoxyvinyl) stannane (71 mg, 0.196 mmol), dimethylamino ethanol (17.9 mg, 0.2 mmol) and Pd(dppf)2Cl2 in NMP (2 ml) was degassed and heated to 100° C. overnight. The crude product was purified by prep-HPLC to give (E)-N-(3-(2-ethoxyvinyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide.

Workup

customwas degassed
customThe crude product was purified by prep-HPLC

Sources & evidence

ORD record: ord-e9b0dc2119444dc39faf782e8ca09162
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461134B2

Reaction notes

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