2-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride) → (3-tert-Butoxycarbonylamino-2'-trifluoromethoxy-biphenyl-4-yl)-carbamic acid tert-butyl ester

HRID 1518136Notes

Reaction equation

[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][C:9]=1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:4])([CH3:3])[CH3:2].[F:24][C:25]([F:37])([F:36])[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O>>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][C:25]([F:24])([F:37])[F:36])=[CH:10][C:9]=1[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 27772042-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)

HCID 130078031,2-Di(tert-Butyloxycarbonylamino)-4-bromobenzene

Product 1

HCID 59280073(3-tert-Butoxycarbonylamino-2'-trifluoromethoxy-biphenyl-4-yl)-carbamic acid tert-butyl ester

Procedure

The title compound was prepared from (4-bromo-2-tert-butoxycarbonylamino-phenyl)-carbamic acid tert-butyl ester (as prepared in the previous step) and 2-trifluoromethoxyphenylboronic acid according to the procedure described in Example 1, step D. 1H-NMR (400 MHz, CDCl3) δ: 7.59 (br. s., 2H), 7.37-7.42 (m, 1H), 7.26-7.34 (m, 3H), 7.24 (dd, J=8.3, 2.0 Hz, 1H), 7.00 (br. s., 1H), 6.94 (br. s., 1H), 1.52 (s, 9H), 1.50 (s, 9H).

Sources & evidence

ORD record: ord-f7ef741085b049bbac51b2bd3cb03e54
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232409B2

Reaction notes

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