Phenylboronic Acid → HCID 71138591, compound

HRID 404189Notes

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].C1(B(O)O)C=CC=CC=1>>[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]([F:12])([F:11])[C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:26][CH:27]=2)=[CH:17][N:18]=1

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 71138867HCID 71138867, compound

Product 1

HCID 71138591HCID 71138591, compound

Procedure

Compound 11 was prepared in a similar manner to compound 5 from phenylboronic acid to afford a solid (30 mg, 8.7%). 1H NMR (500 MHz, CDCl3): δ 8.74 (s, 1H), 8.25 (s, 1H), 7.52 (d, J=8.5 Hz, 1H), 7.49 (br s, 1H), 7.45-7.35 (m, 3H), 7.30-7.29 (m, 1H), 7.28-7.27 (m, 1H), 7.06 (d, J=7.5 Hz, 2H), 6.79-6.74 (m, 1H), 6.72-6.69 (m, 1H), 5.54 (d, J=14.0 Hz, 1H), 5.12 (d, J=14.0 Hz, 1H). MS (ESI): m/z 446.8 [M++1]. HPLC: 99.5%.

Sources & evidence

ORD record: ord-f8a48c3526a0428885755c6450037976
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748461B2

Reaction notes

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