4-Fluorophenylboronic acid → HCID 25056887, compound

HRID 2422493Notes

Reaction equation

HRID 2422493 reaction equation
FC1C=CC(B(O)O)=CC=1.[CH:11]1([C:14]([CH:18]2[CH2:20][CH2:19]2)([OH:17])[C:15]#[CH:16])[CH2:13][CH2:12]1.[N:21]([CH2:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)=[CH:30][C:31](=[O:35])[O:32]2)=[CH:27][CH:26]=1)=[N+:22]=[N-:23]>>[N:21]([CH2:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)=[CH:30][C:31](=[O:35])[O:32]2)=[CH:27][CH:26]=1)=[N+:22]=[N-:23].[CH:11]1([C:14]([CH:18]2[CH2:20][CH2:19]2)([OH:17])[C:15]2[N:23]=[N:22][N:21]([CH2:24][C:25]3[CH:34]=[C:33]4[C:28]([C:29]([C:36]5[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=5)=[CH:30][C:31](=[O:35])[O:32]4)=[CH:27][CH:26]=3)[CH:16]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 2856454-Fluorophenylboronic acidHCID 5201091,1-dicyclopropylprop-2-yn-1-olHCID 866219667-(Azidomethyl)-4-(4-fluorophenyl)-2H-1-benzopyran-2-one

Product 2

HCID 25056887HCID 25056887, compoundHCID 866219667-(Azidomethyl)-4-(4-fluorophenyl)-2H-1-benzopyran-2-one

Procedure

7-(Azidomethyl)-4-(4-fluorophenyl)-2H-chromen-2-one was prepared using the general procedure described in example 1, steps 3-7, but substituting 4-fluorobenzeneboronic acid in place of 3-fluorobenzeneboronic acid. The title compound was prepared using 1,1-dicyclopropylprop-2-yn-1-ol and 7-(azidomethyl)-4-(4-fluorophenyl)-2H-chromen-2-one using the general cycloaddition procedure described in example 12. 1H NMR (400 MHz, acetone-d6): 1H NMR (400 MHz, acetone-d6): 7.95 (s, 1H), 7.7-7.65 (m, 1H), 7.52 (d, 1H), 7.40-7.35 (m, 3H), 7.30 (d, 1H), 6.40 (s, 1H), 5.80 (s, 2H), 3.72 (s, 1H), 1.45-1.35 (m, 2H), 0.55-0.45 (m, 4H), 0.45-0.35 (m, 2H), 0.30-0.20 (m, 2H).

Sources & evidence

ORD record
ord-44bbe0caa84642639b0a87f7ac456e98
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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