(3-Carbamoylphenyl)boronic acid → HCID 68076363, compound

HRID 81875Notes

Reaction equation

HRID 81875 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([C:48]3[CH:53]=[CH:52][C:51](Br)=[CH:50][CH:49]=3)=[CH:44][CH:43]=2)[C:26](=[O:40])[CH2:27][N:28]([CH3:39])[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:55]([C:58]1[CH:59]=[C:60](B(O)O)[CH:61]=[CH:62][CH:63]=1)(=[O:57])[NH2:56]>>[CH2:1]([O:8][C:9]1[CH:24]=[C:23]([N:25]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([C:48]3[CH:53]=[CH:52][C:51]([C:62]4[CH:61]=[CH:60][CH:59]=[C:58]([C:55](=[O:57])[NH2:56])[CH:63]=4)=[CH:50][CH:49]=3)=[CH:44][CH:43]=2)[C:26](=[O:40])[CH2:27][N:28]([CH3:39])[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:22]=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2737814(3-Carbamoylphenyl)boronic acidHCID 89765210benzyl 2-(Benzyloxy)-4-(N-((4'-bromo-[1,1'-biphenyl]-4-yl)methyl)-2-(N,4-dimethylphenylsulfonamido)acetamido)benzoate

Product 1

HCID 68076363HCID 68076363, compoundYield 32%

Procedure

Aryl halide 5 was coupled to 3-carbamoylphenylboronic acid on a 0.1 mmol scale via General Procedure H to give 38 (38 mg, 32%): δH (400 MHz, CDCl3) 2.39 (s, 3H, CH3), 2.83 (s, 3H, CH3), 3.69 (s, 2H, CH2), 4.84 (s, 2H, CH2), 5.03 (s, 2H, CH2), 5.35 (s, 2H, CH2), 6.63 (s, 1H, CH), 6.70 (d, J=8.8 Hz, 1H, CH), 7.19 (d, J=8.0 Hz, 2H, CH), 7.30-7.36 (m, 10H, CH), 7.38-7.41 (m, 3H, CH), 7.54 (d, J=8.0 Hz, 2H, CH), 7.62 (d, J=8.0 Hz, 2H, CH), 7.67 (q, J=7.2 Hz, 4H, CH), 7.79 (t, 2H, J=7.6 Hz, CH), 7.85 (d, J=8.0 Hz, 1H, CH), 8.12 (s, 1H, CH). LRMS (ES+) Calcd for [C51H45N3O7S+Na] 866.29 found 866.51.

Sources & evidence

ORD record
ord-4fa8ece6ffa74cc9825f35d8513a0288
Source dataset
uspto-grants-2014_09
Patent number
US08846707B2

Reaction notes

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