Ammonium Hydroxide → (4-Amino-3-bromothieno[3,2-c]pyridin-7-yl)methanol

HRID 17150Notes

Reaction equation

HRID 17150 reaction equation
C([O:4][CH2:5][C:6]1[C:7]2[S:15][CH:14]=[C:13]([Br:16])[C:8]=2[C:9](Cl)=[N:10][CH:11]=1)(=O)C.[NH4+:17].[OH-]>O1CCOCC1>[NH2:17][C:9]1[C:8]2[C:13]([Br:16])=[CH:14][S:15][C:7]=2[C:6]([CH2:5][OH:4])=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 18450772(3-Bromo-4-chlorothieno[3,2-c]pyridin-7-yl)methyl acetate

Product 1

HCID 18450834(4-Amino-3-bromothieno[3,2-c]pyridin-7-yl)methanolYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 277D (3.1 g, 9.7 mmol), concentrated NH4OH (62 mL), and dioxane (62 mL) was heated to 150° C. in a sealed tube for 36 hours, filtered, and concentrated to provide a soid which was triturated with water (20 mL), collected and dried to give 2.1 g (84% yield) of the desired product. MS (ESI(+)) m/e 258.9, 260.8 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto provide a soid which
  4. customwas triturated with water (20 mL)
  5. customcollected
  6. customdried

Sources & evidence

ORD record
ord-5c447714bb2f4760af08b1846abc489c
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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