Triphenylphosphine → 1-[4-(Aminocarbonyl)-6-chloro-2-pyridinyl]-4-piperidinyl 4-bromo-5-methyl-1H-pyrrole-2-carboxylate

HRID 2233955Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)[N:10]=1)[C:5]([NH2:7])=[O:6].[Br:18][C:19]1[CH:20]=[C:21]([C:25](O)=[O:26])[NH:22][C:23]=1[CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:18][C:19]1[CH:20]=[C:21]([C:25]([O:17][CH:14]2[CH2:15][CH2:16][N:11]([C:9]3[CH:8]=[C:4]([C:5]([NH2:7])=[O:6])[CH:3]=[C:2]([Cl:1])[N:10]=3)[CH2:12][CH2:13]2)=[O:26])[NH:22][C:23]=1[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

2-chloro-6-(4-hydroxypiperidin-1-yl)isonicotinamide (Intermediate 62; 123 mg, 0.48 mmol), 4-bromo-5-methyl-1H-pyrrole-2-carboxylic acid (Intermediate 18) (98 mg, 0.48 mmol) and triphenylphosphine (138 mg, 0.53 mmol) were stirred in anhydrous THF and cooled to 0° C. DEAD (83 μl, 0.53 mmol) was added and the mixture was stirred at room temperature for 18 h. The mixture was filtered, diluted with EtOAc and washed with water and dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography eluting with EtOAc/hexane (4:1) to afford the title compound (11 mg).

Workup

filtrationThe mixture was filtered
additiondiluted with EtOAc
washwashed with water
dry with materialdried over sodium sulphate
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography
washeluting with EtOAc/hexane (4:1)

Sources & evidence

ORD record: ord-ea6c5af72e6d4271ba187d29b02a0df9
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709503B2

Reaction notes

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