4-(4-BOC-Piperazino)phenylboronic acid → HCID 59424537, compound

HRID 500818Notes

Reaction equation

HRID 500818 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17](S(C)(=O)=O)=[CH:16][CH:15]=3)[S:13][C:6]=12.[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][N:41](C2C=CC(B(O)O)=CC=2)[CH2:40][CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>>[F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([N:41]4[CH2:40][CH2:39][N:38]([C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:37])[CH2:43][CH2:42]4)=[CH:18][CH:19]=3)[S:13][C:6]=12

Participants

3

Reactant 2

HCID 52330144-(4-BOC-Piperazino)phenylboronic acidHCID 587728787-(2-Fluoro-4-nitrophenoxy)-2-(4-(methylsulfonyl)phenyl)thieno[3,2-b]pyridine

Product 1

HCID 59424537HCID 59424537, compoundYield 70%

Procedure

Starting from the nitro-bromo compound 42, following the procedure described above for the synthesis of compound 48 (scheme 10, example 55) but substituting 4,4,5,5-tetramethyl-2-(4-(methylsulfonyl)phenyl)-1,3,2-dioxaborolane for 4-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenylboronic acid, title compound 156 was obtained in 70% yield. LRMS (M+1) 550.6 (100%).

Sources & evidence

ORD record
ord-0fed0d1d813642eca888087952f1f1e4
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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