Methylboronic Acid → HCID 58465102, compound

HRID 2089454Notes

Reaction equation

[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9](Br)[C:8]=2[F:14])=[N:4][C:3]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][N:21]([CH3:31])[C:22]=1[N:23]1[CH2:29][CH2:28][CH2:27][C@@H:26]([NH2:30])[CH2:25][CH2:24]1)=[O:16].[CH3:32]B(O)O>>[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH3:32])[C:8]=2[F:14])=[N:4][C:3]=1[C:15]([NH:17][C:18]1[CH:19]=[N:20][N:21]([CH3:31])[C:22]=1[N:23]1[CH2:29][CH2:28][CH2:27][C@@H:26]([NH2:30])[CH2:25][CH2:24]1)=[O:16]

Participants

Reactant 2

HCID 139377Methylboronic Acid

HCID 58464936HCID 58464936, compound

Product 1

HCID 58465102HCID 58465102, compound

Procedure

Boc and Cbz protected intermediate of 373 from Example 373, was subjected to standard Suzuki conditions, following procedures in Example 141 with methyl boronic acid to give the methylated intermediate. Deprotection according to procedures for Example 373, gave 381. 1H NMR (400 MHz, DMSO) δ 8.89 (s, 1H), 8.07 (t, J=7.2 Hz, 1H), 7.52 (s, 1H), 7.40 (s, 2H), 7.32 (t, J=6.9 Hz, 1H), 7.22 (t, J=7.7 Hz, 1H), 6.74 (s, 1H), 3.65 (s, 4H), 3.23-2.95 (m, 8H), 2.31 (s, 3H), 1.95-1.72 (m, 4H), 1.72-1.44 (m, 4H). MS (ESI) m/z: 444.2 [M+H+].

Workup

customto give the methylated intermediate

Sources & evidence

ORD record: ord-e63f59c150414b81ac50f50ddaab7eeb
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436001B2

Reaction notes

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