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

HRID 1910088Notes

Reaction equation

HRID 1910088 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[C:12]([F:27])=[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>>[F:27][C:12]1[C:11]([C:8]2[C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][C:6]=3[O:10][CH:9]=2)=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH2:15][NH:16]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 668239041,1-dimethylethyl 5-(4-aminofuro[3,2-c]pyridin-3-yl)-4-fluoro-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 668240273-(4-fluoro-2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amineYield 100%

Procedure

A mixture of 1,1-dimethylethyl 5-(4-aminofuro[3,2-c]pyridin-3-yl)-4-fluoro-2,3-dihydro-1H-indole-1-carboxylate (205 mg, 0.555 mmol) and HCl, 4.0 M in dioxane (2775 μl, 11.10 mmol) was stirred at room temperature under Nitrogen for 16 hr. The reaction mixture was then concentrated in vacuo to give 3-(4-fluoro-2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine (226 mg, 0.555 mmol, 100% yield) as an off-white solid. LC/MS (ES) m/z=270 [M+H]+.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-822dc4baad7b41fca577310c04de987c
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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