4-Chloroquinoline → HCID 49806029, compound

HRID 241096Notes

Reaction equation

HRID 241096 reaction equation
F[C:2](F)(F)[C:3]([O-:5])=O.[S:8]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9]1.Cl[C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[CH:19][CH:18]=1>>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]([N:20]2[CH2:19][C:18]3[CH:17]=[C:26]([C:10]4[CH:11]=[CH:12][S:8][CH:9]=4)[CH:25]=[CH:2][C:3]=3[O:5][CH2:22][CH2:21]2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 691404-ChloroquinolineHCID 84468TrifluoroacetateHCID 581760Thiophene-3-boronic acid

Product 1

HCID 49806029HCID 49806029, compound

Procedure

Prepared as the trifluoroacetate salt according to the method of example 3 by using thiophen-3-ylboronic acid in step 1 and 4-chloroquinoline in step 3. 1H NMR (400 MHz, d6-DMSO): 8.56 (d, 1H), 8.32 (d, 1H), 8.01-7.91 (m, 3H), 7.85 (s, 1H), 7.71-7.65 (m, 2H), 7.63-7.58 (m, 2H), 6.97-6.91 (m, 2H), 5.25 (s, 2H), 4.60 (t, 2H), 4.40 (t, 2H); MS (EI) for C22H18N2OS: 359 (MH+).

Sources & evidence

ORD record
ord-f3006e9f83ea49d680d8317bd7a7bcac
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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