2-Bromopyridine → HCID 117601099, compound

HRID 1773725Notes

Reaction equation

HRID 1773725 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[NH2:13][C:14]1[C:23]([NH2:24])=[CH:22][C:21]([C:25]2[C:26]([CH3:31])=[N:27][O:28][C:29]=2[CH3:30])=[CH:20][C:15]=1[C:16]([O:18]C)=O.CN1C2C(N=C(N)NC=2NCC1CNC1C=CC([C:53]([NH:55][CH:56](C(O)=O)[CH2:57][CH2:58][C:59](O)=O)=O)=CC=1)=O>>[NH2:13][C:14]1[C:23]([NH2:24])=[CH:22][C:21]([C:25]2[C:26]([CH3:31])=[N:27][O:28][C:29]=2[CH3:30])=[CH:20][C:15]=1[C:16]([C:56]1[CH:57]=[CH:58][CH:59]=[CH:53][N:55]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[OH:18]

Participants

5

Reactant 4

HCID 79732-BromopyridineHCID 117601650HCID 117601650, compoundHCID 178418339ButyllithiumHCID 178479889HCID 178479889, compound2×

Product 1

HCID 117601099HCID 117601099, compound

Procedure

Butyllithium (1.6M solution in hexanes, 24 mL, 38 mmol) was added dropwise over 20 minutes to a solution of 2-bromopyridine (3.7 mL, 38 mmol in methyl-THF (100 mL) at −78° C. The reaction mixture was stirred for 1 hour and a solution of methyl 2,3-diamino-5-(3,5-dimethylisoxazol-4-yl)benzoate (2.0 g, 7.7 mmol) in 20 mL of methyl-THF was added. The reaction mixture was warmed to room temperature, stirred for 30 minutes and quenched with water. The reaction mixture was extracted with ethyl acetate and purified by silica gel chromatography (90:9:1 ethyl acetate/methanol/ammonium hydroxide) to give (2,3-diamino-5-(3,5-dimethylisoxazol-4-yl)phenyl)di(pyridin-2-yl)methanol as an orange powder.

Workup

  1. stirringstirred for 30 minutes
  2. customquenched with water
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. custompurified by silica gel chromatography (90:9:1 ethyl acetate/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-af6c8d34fdae4db4b700b57ce08c3851
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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