Boronic Acid → (2-fluoro-3-hydroxy-phenyl)-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 1098481Notes

Reaction equation

HRID 1098481 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:14]=3[F:20])=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.BrC1C=C2C(C([C:33]3[CH:38]=[CH:37][CH:36]=[C:35](O)[C:34]=3C)=O)=CNC2=NC=1.C1(B(O)O)C=CC=CC=1.B(O)O>>[F:20][C:14]1[C:15]([OH:19])=[CH:16][CH:17]=[CH:18][C:13]=1[C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH:3]=2)[NH:8][CH:9]=1)=[O:12]

Participants

5

Reactant 4

HCID 61668Boronic AcidHCID 66827Phenylboronic AcidHCID 58086399(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-fluoro-3-hydroxy-phenyl)-methanoneHCID 58086486(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(3-hydroxy-2-methyl-phenyl)-methanone

Product 1

HCID 58086274(2-fluoro-3-hydroxy-phenyl)-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Procedure

Additional compounds were prepared following the protocol of Scheme 11, optionally replacing (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-fluoro-3-hydroxy-phenyl)-methanone P-0067 with (5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(3-hydroxy-2-methyl-phenyl)-methanone P-0055 (prepared as described in Example 56, Scheme 22) in Step 1 and optionally replacing phenylboronic acid with an appropriate boronic acid in Step 2. The following compounds were made following this procedure:

Workup

  1. customAdditional compounds were prepared

Sources & evidence

ORD record
ord-d4c66afc1f67455fa14fea14fcf8ae0e
Source dataset
uspto-grants-2012_03
Patent number
US08143271B2

Reaction notes

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