4-Fluorobenzaldehyde → HCID 22341802, compound

HRID 584775Notes

Reaction equation

HRID 584775 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O)=[O:11].[NH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30](=[O:35])[CH:31]=C(C)C>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:21]2[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[NH:29][C:30](=[O:35])[CH:31]2[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:10]=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 2921892-Formylphenylboronic acidHCID 20821695HCID 20821695, compound

Product 1

HCID 22341802HCID 22341802, compound

Procedure

Prepared similarly to Example 3 with reductive amination using 4-fluorobenzaldehyde, and the use of 2-formylphenylboronic acid. Prepared in 34% overall yield without isolation of intermediates starting from the product of Example 1. 1H NMR (500 MHz, DMSO-d6) δ 10.37 (s, 1H), 7.83-7.79 (m, 1H), 7.64-7.60 (m, 1H), 7.40-7.34 (m, 2H), 7.29-7.19 (m, 3H), 7.70-6.95 (m, 5H), 6.32 (s, 1H), 5.09 (d, J=15.4 Hz, 1H), 5.01 (d, J=15.4 Hz, 1H), 4.56 (d, J=15.3 Hz, 1H), 4.47 (d, J=15.3 Hz, 1H).

Workup

  1. customPrepared similarly to Example 3 with reductive
  2. customPrepared in 34%
  3. customoverall yield without isolation of intermediates

Sources & evidence

ORD record
ord-d6611bbd76e74ba8b99f4a4dab0cc0e7
Source dataset
uspto-grants-2005_08
Patent number
US06927294B1

Reaction notes

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