1,4-Dioxane → 3-(2,3-dihydro-1H-indol-5-yl)thieno[3,2-c]pyridin-4-amine

HRID 1909942Notes

Reaction equation

HRID 1909942 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][S:10][C:6]=2[CH:5]=[CH:4][N:3]=1.O1CCOCC1>Cl>[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[S:10][CH:9]=3)=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 668238131,1-dimethylethyl 5-(4-aminothieno[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 668235693-(2,3-dihydro-1H-indol-5-yl)thieno[3,2-c]pyridin-4-amineYield 91.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1,1-dimethylethyl 5-(4-aminothieno[3,2-c]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate (5.19 g, 14.12 mmol) was taken up in 4 M HCl in dioxane (100 ml, 400 mmol) as a slurry and left to stir at room temperature overnight. The reaction was then filtered and washed with dioxane to afford 3-(2,3-dihydro-1H-indol-5-yl)thieno[3,2-c]pyridin-4-amine (3.44 g) as an off white solid. LC/MS (ES) m/z=268.1 [M+H]+

Workup

  1. waitleft
  2. filtrationThe reaction was then filtered
  3. washwashed with dioxane

Sources & evidence

ORD record
ord-df0dd934e0a34d75a2758c85878ab0d7
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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