2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester → HCID 57387165, compound

HRID 1771468Notes

Reaction equation

HRID 1771468 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([F:12])=[C:7]([OH:13])[CH:6]=[CH:5]2.[CH3:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=1B1OC(C)(C)C(C)(C)O1)[C:18]([O:20]C)=[O:19]>>[F:12][C:8]1[C:7]([OH:13])=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([C:24]1[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=1[CH3:14])=[CH:3]2

Participants

3

Reactant 2

HCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterHCID 112419406-Bromo-1-fluoronaphthalen-2-OL2×

Product 1

HCID 57387165HCID 57387165, compound

Procedure

Followed the coupling procedure described in Example 29 starting from 6-bromo-1-fluoronaphthalen-2-ol (Intermediate 13) and methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate. 1H-NMR (DMSO-d6, 300 MHz, TMS): δ 12.90 (b, 1H), 10.17 (b, 1H), 7.84-7.97 (m, 4H), 7.70 (d, 1H), 7.54 (d, 1H), 7.41 (d, 1H), 7.30 (t, 1H), 2.33 (s, 3H). MS (ESI): m/z=295.25 [MA]−.

Sources & evidence

ORD record
ord-c6877a8e72574267a473e52d54b33cb5
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

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