Acetaldehyde → 5-Bromo-N-ethylpyridin-2-amine

HRID 1814173Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH:9](=O)[CH3:10].COC(=O)COC1C=C(OC)C(SCCCN(CC)C2C=CC(C3C=CC=CC=3)=CN=2)=CC=1C>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][CH3:10])=[N:6][CH:7]=1

Participants

Reactant 3

HCID 177Acetaldehyde

HCID 706222-Amino-5-bromopyridine

HCID 20770817(4-{3-[Ethyl-(5-phenyl-pyridin-2-yl)-amino]-propylsulfanyl}-5-methoxy-2-methyl-phenoxy)-acetic acid methyl ester

Product 1

HCID 225049165-Bromo-N-ethylpyridin-2-amine

Procedure

5-Bromo-pyridin-2-ylamine and acetaldehyde were treated under the conditions of Compound 64C to give the intermediate (5-bromo-pyridin-2-yl)-ethyl-amine. This was then reacted with Compound 64A to give the title product. MS m/z 481 (M+1). Step 2. Preparation of (4-{3-[(5-Bromo-pyridin-2-yl)-ethyl-amino]-propylsulfanyl]-5-methoxy-2-methyl-phenoxy}-acetic acid (Compound 68)

Sources & evidence

ORD record: ord-86227d7a55df405cad7e7e348ac6ed30
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875780B2

Reaction notes

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