Morpholine → 5-Benzyloxy-2-(morpholine-4-carbon yl)-pyrrolo[2,3-b]pyridine-1-carboxylic Acid tert-butyl Ester

HRID 1437705Notes

Reaction equation

HRID 1437705 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[C:11]2[CH:10]=[C:9]1[C:25](O)=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[NH:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:16]=[C:11]2[CH:10]=[C:9]1[C:25]([N:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1)=[O:26])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 684251515-Benzyloxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester2×

Product 1

HCID 684251095-Benzyloxy-2-(morpholine-4-carbon yl)-pyrrolo[2,3-b]pyridine-1-carboxylic Acid tert-butyl EsterYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was synthesized in analogy to example 9, intermediate a), from 5-benzyloxy-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester (intermediate G), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, morpholine and N,N-diisopropylethylamine in DMF to give the desired product as colorless foam (70%).

Sources & evidence

ORD record
ord-ab2dd8c7500c44daae91c8e76a05ba7c
Source dataset
uspto-grants-2009_11
Patent number
US07622466B2

Reaction notes

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