Cesium carbonate → Methyl 2-(6-bromopyridin-3-ylamino)-5-cyclopropylbenzoate

HRID 42005Notes

Reaction equation

HRID 42005 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:14][CH2:13]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][N:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[Br:15][C:16]1[N:17]=[CH:18][C:19]([NH:1][C:2]2[CH:11]=[CH:10][C:9]([CH:12]3[CH2:14][CH2:13]3)=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:20][CH:21]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 47382712-Bromo-5-iodopyridineHCID 13052309Methyl 2-amino-5-cyclopropylbenzoate2×

Product 1

HCID 86657257Methyl 2-(6-bromopyridin-3-ylamino)-5-cyclopropylbenzoate

Procedure

Obtained (0.155 g, 43% of yield) following the procedure described in Intermediate 15 starting with methyl 2-amino-5-cyclopropylbenzoate (described in Intermediate 8 (step A)) (1.05 mmol, 0.200 g), 2-bromo-5-iodopyridine (1.05 mmol, 0.297 g) and Cs2CO3 (2.09 mmol, 0.682 g) instead of NaOtBu.

Workup

  1. customObtained
  2. custom(0.155 g, 43% of yield)

Sources & evidence

ORD record
ord-76baa274cfbe43e591e96d19e787b44a
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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