Hydrochloric Acid → 4-(2-Amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid

HRID 595941노트

반응식

HRID 595941 반응식
[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([Br:19])=[CH:4][N:3]=1.[Li+].[OH-].Cl.CCOC(C)=O>C1COCC1.CO>[NH2:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:6][C:5]([Br:19])=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 118045477Methyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate

생성물 1

HCID 1180467884-(2-Amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoate (1.9 g, 5.84 mmol) in THF (19.48 mL) and MeOH (9.74 mL, Ratio: 1.000) was added LiOH (1 M aqueous solutionueous solution) (10.52 mL, 10.52 mmol). The reaction mixture was stirred for 5 h. After 1N HCl (1.9 mL) was added up to pH 5, the reaction mixture was worked up with EtOAc, the organic layer was dried over Na2SO4, filtered off and concentrated in vacuo. The crude 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid was used for the next step without further purification. LCMS (m/z): 311.1/313.1 (MH+), 0.5 min.

후처리

  1. dry with materialthe organic layer was dried over Na2SO4
  2. filtrationfiltered off
  3. concentrationconcentrated in vacuo
  4. customThe crude 4-(2-amino-5-bromopyridin-3-yl)-2-fluorobenzoic acid was used for the next step without further purification
  5. custom311.1/313.1 (MH+), 0.5 min.

출처 및 근거

ORD 기록
ord-fa4c0f59979c4c3fbde172247a9d4431
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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