Potassium Carbonate → [4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetic acid methyl ester

HRID 731046Notes

Reaction equation

HRID 731046 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][C:17]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[CH:16][C:15]=2[C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:35][C:36]([O:38][CH3:39])=[O:37]>CC(C)=O>[CH3:39][O:38][C:36](=[O:37])[CH2:35][O:27][C:24]1[CH:23]=[CH:22][C:21]([C:17]2[CH:18]=[CH:19][C:20]3[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:9]4[CH2:10][CH2:11][CH2:12][CH2:13][C:14]=4[C:15]=3[CH:16]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 688142534-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenol

Product 1

HCID 68814354[4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenoxy]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The desired product was prepared using a procedure similar to step 1 of example 4. Thus, 4-(9-benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenol (0.419 g, 1.185 mmol) was reacted with K2CO3 (0.213 g, 1.541 mmol) and methyl bromoacetate (0.236 g, 1.541 mmol) in acetone to give the product (0.362 g, 0.851 mmol, 72%) as a white solid, mp 109-112° C. 1H NMR (DMSO-d6) δ 1.77-1.87 (m, 4H), 2.65 (t, J=5.3 Hz, 2H), 2.70 (t, J=6.0 Hz, 2H), 3.71 (s, 3H), 4.81 (s, 2H), 5.33 (s, 2H), 6.98 (d, J=8.7 Hz, 2H), 7.03 (d, J=7.3 Hz, 2H), 7.21 (t, J=7.2 Hz, 1H), 7.25-7.30 (m, 3H), 7.39 (d, J=8.4 Hz, 1H), 7.57 (d, J=8.7 Hz, 2H), 7.58 (d, J=1.1 Hz, 1H); [ESI(+)], m/z 426 (M+H)+.

Sources & evidence

ORD record
ord-40d704bd7b794ac0b97fb3e246f77e08
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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