Potassium Bromide → {6-Methyl-8-[4-(5-trifluoromethyl-pyridine-2-yl)-benzylsulfanyl]-chroman-5-yloxy}-acetic acid

HRID 1591552Notes

Reaction equation

HRID 1591552 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[C:15]([CH3:16])=[CH:14][C:13]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][N:26]=3)=[CH:21][CH:20]=2)=[C:12]2[C:7]=1[CH2:8][CH2:9][CH2:10][O:11]2.COC(=O)COC1C(C)=CC(S)=C2C=1CCCO2.ClCC1C=CC(C2C=CC(C(F)(F)F)=CN=2)=CC=1.[K+].[Br-]>>[CH3:16][C:15]1[C:6]([O:5][CH2:4][C:3]([OH:35])=[O:2])=[C:7]2[C:12](=[C:13]([S:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:27][N:26]=4)=[CH:23][CH:24]=3)[CH:14]=1)[O:11][CH2:10][CH2:9][CH2:8]2

Participants

5

Reactant 4

HCID 253877Potassium BromideHCID 20827065{6-Methyl-8-[4-(5-trifluoromethyl-pyridine-2-yl)-benzylsulfanyl]-chroman-5-yloxy}-acetic acid methyl ester5×HCID 222800672-[4-(Chloromethyl)phenyl]-5-(trifluoromethyl)pyridineHCID 22603275(8-Mercapto-6-methyl-chroman-5-yloxy)-acetic acid methyl ester

Product 1

HCID 22280197{6-Methyl-8-[4-(5-trifluoromethyl-pyridine-2-yl)-benzylsulfanyl]-chroman-5-yloxy}-acetic acid

Procedure

{6-Methyl-8-[4-(5-trifluoromethyl-pyridine-2-yl)-benzylsulfanyl]-chroman-5-yloxy}-acetic acid methyl ester (compound 36A) The title compound was prepared in the manner analogous to Example 1F using (8-mercapto-6-methyl-chroman-5-yloxy)-acetic acid methyl ester and 18B. MS m/z 504 (M+1). Step 2. {6-Methyl-8-[4-(5-trifluoromethyl-pyridine-2-yl)-benzylsulfanyl]-chroman-5-yloxy}-acetic acid methyl ester (compound 36) The title compound was prepared in the manner analogous to Example 1 using 36A. mp 156-157° C.; IR (KBr) cm−1: 2928, 1731, 1710, 1603, 1329, 1113, 1082; 400 MHz 1H NMR (DMSO-d6): δ 12.84 (br(s), 1H), 8.97 (s, 1H), 8.22 (dd, 1H, J=8.4, 2.0 Hz), 8.12 (d, 1H, J=8.4 Hz), 8.04 (d, 2H, J=8.2 Hz), 7.42 (d, 2H, J=8.2 Hz), 6.88 (s, 1H), 4.29 (s, 2H), 4.05-4.14 (m, 4H), 2.64 (t, 2H, J=6.3 Hz), 2.04 (s, 3H), 1.81 (pentet, 2H); MS m/z 490 (M+1). Anal. Calc'd for C25H22F3NO4S: C, 61.34; H, 4.53; N, 2.86; found: C, 60.96; H, 4.48; N, 2.79.

Sources & evidence

ORD record
ord-2c3e42cb1aad428685593ee13cc18f11
Source dataset
uspto-grants-2007_11
Patent number
USRE039916E1

Reaction notes

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