Bromoacetonitrile → 2-((5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)methoxy)acetonitrile

HRID 931558Notes

Reaction equation

HRID 931558 reaction equation
[NH2:1][C:2]1([CH2:18][OH:19])[C:15]2[C:10](=[N:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[O:9][C:8]2[C:3]1=[CH:4][C:5]([I:17])=[CH:6][CH:7]=2.Br[CH2:21][C:22]#[N:23].CC(C)([O-])C.[Li+]>C1COCC1>[NH2:1][C:2]1([CH2:18][O:19][CH2:21][C:22]#[N:23])[C:15]2[C:10](=[N:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[O:9][C:8]2[C:3]1=[CH:4][C:5]([I:17])=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)HCID 67382607(5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)methanol

Product 1

HCID 673826922-((5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)methoxy)acetonitrileYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)methanol (10.00 g, 23.09 mmol) and bromoacetonitrile (12.06 mL, 173 mmol) in 25 mL THF was heated to 40° C. Lithium tert-butoxide [1N in THF (173 mL, 173 mmol)] was added drop wise via addition funnel over 5 hours. After completed addition, the reaction mixture was concentrated. The residue was purified by column chromatography [0-80% (95:5 EtOAc/MeOH)/heptane] to yield 2-((5-amino-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)methoxy)acetonitrile (5.58 g, 11.82 mmol, 51.2% yield).

Workup

  1. additionwise via addition funnel over 5 hours
  2. additionaddition
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was purified by column chromatography [0-80% (95:5 EtOAc/MeOH)/heptane]

Sources & evidence

ORD record
ord-ca46ef80fb214b0299ce7c753fb404cb
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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