Pyrrole-2-carboxaldehyde → HCID 136495273, compound

HRID 931686Notes

Reaction equation

HRID 931686 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH:8]([P:11]([CH:15]([CH3:17])[CH3:16])[CH2:12][CH2:13][NH2:14])([CH3:10])[CH3:9]>>[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[N:14][CH2:13][CH2:12][P:11]([CH:15]([CH3:17])[CH3:16])[CH:8]([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 13854Pyrrole-2-carboxaldehydeHCID 575529962-[Di(propan-2-yl)phosphanyl]ethan-1-amine

Product 1

HCID 136495273HCID 136495273, compoundYield 97.2%

Procedure

Replicate the preparation of the ligand used in Ex. 7 except use 0.2 g (2.103 mmol) of pyrrole-2-carbaldehyde and use adding 0.356 g (2.208 mmol) of 2-(di-isopropylphosphino)ethanamine instead of N1,N1-dimethylethane-1,2-diamine to give 0.487 g (97%) of N-((1H-pyrrol-2-yl)methylene)-2-(di(propan-2-yl)phosphino)ethanamine as a colorless, semi solid, which is analytically pure by GC-MS and 1H-NMR: 1H NMR (400 MHz, Benzene): δ 10.05 (s, 1H), 7.83 (s, 1H), 6.51 (s, 1H), 6.44 (m, J=2.2 Hz, 1H), 6.28-6.14 (m, 1H), 3.67 (dd, J=15.2, 6.9 Hz, 2H), 1.75-1.64 (m, 2H), 1.58 (dq, J=6.9, 5.3 Hz, 2H), 1.00 (ddd, J=14.8, 12.3, 7.1 Hz, 12H).

Workup

  1. customthe preparation of the ligand

Sources & evidence

ORD record
ord-a631931334ab49b88bd25551a61c32ac
Source dataset
uspto-grants-2016_03
Patent number
US09296836B2

Reaction notes

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