Hydrochloric Acid → 3-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine

HRID 1909973Notes

Reaction equation

HRID 1909973 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:12]=[C:13]4[C:17](=[CH:18][CH:19]=3)[N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]4)=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1.Cl.O1CCOCC1>>[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([C:8]3[C:7]4[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][C:6]=4[O:10][CH:9]=3)=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 668240741,1-dimethylethyl 5-(4-aminofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 668234823-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amineYield 96.3%

Procedure

A mixture of 1,1-dimethylethyl 5-(4-aminofuro[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate (1.04 g, 2.96 mmol) and HCl, 4.0 M in dioxane (15 mL, 60.0 mmol) was stirred at room temperature under Nitrogen for 4.5 hr. The reaction mixture was then concentrated in vacuo to give 3-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine (973 mg, 2.85 mmol, 96% yield) dihydrochloride (2HCl) as an off-white solid. LC/MS (ES) m/z=252 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-c073b71d924d4c8aaa977df735c5cf3e
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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