Diisopropylethylamine → 2-Chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-vinyl-benzamide

HRID 60558

Reaction equation

HRID 60558 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]=[CH2:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[NH2:47][C:48]1[CH:49]=[CH:50][C:51]2[C:55]([CH3:57])([CH3:56])[O:54][B:53]([OH:58])[C:52]=2[CH:59]=1>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]=[CH2:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:47][C:48]1[CH:49]=[CH:50][C:51]2[C:55]([CH3:56])([CH3:57])[O:54][B:53]([OH:58])[C:52]=2[CH:59]=1)=[O:6]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58373146HCID 58373146, compoundHCID 669277036-aMino-3,3-diMethylbenzo[c][1,2]oxaborol-1(3H)-ol

Product 1

HCID 669274352-Chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-vinyl-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-4-vinyl benzoic acid (44 mg, 0.24 mmol) in DMF (2 mL) was added HATU (55 mg, 0.15 mmol) and DIEA (25 mg, 0.21 mmol). After 1 hour 6-amino-3,3-dimethyl-3H-benzo[c][1,2]oxaborol-1-ol hydrochloride salt (30 mg, 0.14 mmol) was added. After 12 hours the reaction was concentrated down under reduced pressure onto celite. The crude material was subjected to flash chromatography (Isco Companion, 4 g SiO2 cartridge, SiO2 solid load, neat DCM to 10% MeOH gradient) to give 2-Chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-vinyl-benzamide as a white powder. Amount obtained: 20.8 mg (48%). Data: LCMS (M/Z): 342 (M+H); 1H NMR (DMSO-d6) δ: 1.36-1.59 (m, 6 H) 5.42 (d, J=11.1 Hz, 1 H) 6.02 (d, J=17.8 Hz, 1 H) 6.79 (dd, J=17.7, 11.0 Hz, 1 H) 7.33-7.46 (m, 1 H) 7.56 (s, 2 H) 7.69 (d, J=1.6 Hz, 2 H) 8.05 (dd, J=1.7, 0.5 Hz, 1 H) 9.00 (br. s, 1 H) 10.35-10.62 (m, 1 H).

Workup

  1. concentrationAfter 12 hours the reaction was concentrated down under reduced pressure onto celite

Sources & evidence

ORD record
ord-bdc28bb7c78b43e68c7b40bf777bbe32
Source dataset
uspto-grants-2016_09
Patent number
US09440994B2

Linked notes

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