3-(Trifluoromethyl)phenylboronic acid → HCID 58424631, compound

HRID 2096428Notes

Reaction equation

[NH2:1][C:2]1[N:3]([CH3:24])[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13](Br)[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1>O1CCOCC1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:1][C:2]1[N:3]([CH3:24])[C:4](=[O:23])[C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:31]4[CH:30]=[CH:29][CH:28]=[C:27]([C:26]([F:37])([F:36])[F:25])[CH:32]=4)[CH:14]=3)[O:9][CH:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:7]2)[N:6]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Pd(PPh3)2Cl2 (10 mg) in a 10 mL CEM test tube under Ar was treated sequentially with 2′-amino-6-bromo-1′-methyl-2-phenylspiro[chroman-4,4′-imidazol]-5′(1′H)-one (20 mg, 0.052 mmol) in 1,4-dioxane (1 mL), Cs2CO3 (2 N, 0.3 mL) and 3-(trifluoromethyl)phenylboronic acid (19.7 mg, 0.1 mmol). The mixture was heated under microwave at 120° C. for 30 minutes. The reaction mixture was concentrated in vacuo to give the residue, which was purified by preparative TLC and preparative HPLC to give pure 2′-amino-1′-methyl-2-phenyl-6-(3-(trifluoromethyl)phenyl)spiro[chroman-4,4′-imidazol]-5′(1′H)-one (4.31 mg, 18%). 1H-NMR (CDCl3): 1.95 (d, 1H), 2.66 (t, 1H), 3.16 (d, 3H), 5.97 (d, 1H), 6.96 (s, 1H), 7.06 (m, 2H), 7.20 (s, 1H), 7.38 (m, 3H), 7.44 (m, 3H), 7.53 (m, 1H), 7.62 (m, 1H), 7.70 (s, 1H).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customto give the residue, which
customwas purified by preparative TLC and preparative HPLC

Sources & evidence

ORD record: ord-05cd7035c95344f89f66f16169c9e90e
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450308B2

Reaction notes

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