(1H-Pyrrolo[2,3-b]pyridin-2-yl)methanamine → (1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanamine

HRID 1890535Notes

Reaction equation

HRID 1890535 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH2:10][NH2:11].[CH3:12][Si:13]([CH3:32])([CH3:31])[CH2:14][CH2:15][O:16][CH2:17]N1C2=NC=CC=C2C=C1C(OC)=O.Cl.S1C2C=CN=CC=2C=C1CN>>[CH3:12][Si:13]([CH3:32])([CH3:31])[CH2:14][CH2:15][O:16][CH2:17][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH2:10][NH2:11]

Participants

4

Reactant 3

HCID 67305381(1H-Pyrrolo[2,3-b]pyridin-2-yl)methanamineHCID 67306524Methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylateHCID 67306703Thieno[3,2-c]pyridin-2-ylmethanamine hydrochloride

Product 1

HCID 67306119(1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanamine

Procedure

Intermediate H′ was prepared from methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (H′-1) following similar procedures for synthesizing intermediate D from D-2, as described above. MS (m/z): 278 (M+1)+.

Sources & evidence

ORD record
ord-ae4b69bc47484503aff0fff367f26e3e
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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