2-(6-Chloro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline → 2-(5-chloro-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-1,2,3,4-tetrahydro-isoquinoline

HRID 1445132Notes

Reaction equation

HRID 1445132 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9]2)[C:5]([N+:18]([O-])=O)=[CH:4][CH:3]=1.[C:21]([Mg]Br)([CH3:23])=[CH2:22]>>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:22]=[C:21]([CH3:23])[NH:18][C:5]2=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9]2)[N:7]=1

Participants

3

Reactant 2

HCID 431526772-(6-Chloro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinolineHCID 178456138HCID 178456138, compound

Product 1

HCID 866152762-(5-chloro-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-1,2,3,4-tetrahydro-isoquinoline

Procedure

In accordance with the same procedures as in Step 3 of Example 642, except for using 2-(6-chloro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline prepared in Preparation 7 and isopropenylmagnesium bromide, the titled compound was obtained as yellow oil. (Yield: 35%) The product was used in the subsequent step without further purification.

Sources & evidence

ORD record
ord-54bb5fa3e7994a6bb1a1c501b8984102
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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