4-Chlorophenylboronic acid → HCID 71138991, compound

HRID 1506596Notes

Reaction equation

HRID 1506596 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:34])([CH2:28][N:29]1[CH:33]=[N:32][N:31]=[N:30]1)[C:10]([C:13]1[N:18]=[CH:17][C:16]([O:19][C:20]2[CH:27]=[CH:26][C:23](C#N)=[CH:22][CH:21]=2)=[CH:15][CH:14]=1)([F:12])[F:11].[Cl:35]C1C=CC(B(O)O)=CC=1>>[Cl:35][C:23]1[CH:26]=[CH:27][C:20]([O:19][C:16]2[CH:15]=[CH:14][C:13]([C:10]([F:12])([F:11])[C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])([OH:34])[CH2:28][N:29]3[CH:33]=[N:32][N:31]=[N:30]3)=[N:18][CH:17]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 71138867HCID 71138867, compound

Product 1

HCID 71138991HCID 71138991, compound

Procedure

Compound 7 was prepared in a similar manner to compound 5 from (4-chlorophenyl)boronic acid to afford a solid (50 mg, 0.1 mmol, 35.7%). 1H NMR (500 MHz, CDCl3): δ 8.73 (s, 1H), 8.22 (d, J=2.5 Hz, 1H), 7.54 (d, J=8.5 Hz, 1H), 7.46-7.37 (m, 3H), 7.30 (dd, J=3.0, 9.0 Hz, 1H), 7.04-7.00 (m, 2H), 6.80-6.77 (m, 1H), 6.76-6.71 (m, 1H), 5.49 (d, J=14.5 Hz, 1H), 5.16 (d, J=14.5 Hz, 1H). MS (ESI): m/z 479 [M++1]. HPLC: 98.43%.

Sources & evidence

ORD record
ord-4233661385fe463a881c7187aa6ff61b
Source dataset
uspto-grants-2015_12
Patent number
US09220265B2

Reaction notes

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