1,2-Dimethoxyethane → HCID 68749804, compound

HRID 390369Notes

Reaction equation

Br[C:2]1[S:6][C:5]([N:7]2[CH2:12][CH2:11][C:10]3([CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[O:13]3)[CH2:9][CH2:8]2)=[N:4][CH:3]=1.FC1C=CC(C2C3C(=CC=CC=3)OC3(CC[NH:41][CH2:40]C3)C=2)=CC=1.Br[C:52]1S[C:54](Br)=[CH:55][N:56]=1.[C:58]([O-:61])([O-])=[O:59].[K+].[K+].C[O:65]CCOC>C(Cl)Cl>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[O:13][C:10]3([CH2:11][CH2:12][N:7]([C:5]4[S:6][C:2]([N:56]5[CH:55]=[CH:54][N:41]([CH2:40][C:58]([OH:61])=[O:59])[C:52]5=[O:65])=[CH:3][N:4]=4)[CH2:8][CH2:9]3)[CH:21]=2)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Step 3 1′-(5-Bromothiazol-2-yl)-4-(4-fluorophenyl)spiro[chromene-2,4′-piperidine] In a pressure vial, a mixture of 4-(4-fluorophenyl)spiro[chromene-2,4′-piperidine] (233 mg, 0.79 mmol), 2,5-dibromothiazole (279 mg, 1.15 mmol) and K2CO3 (190 mg, 1.38 mmol) was suspended in dry DME (3.5 mL). The reaction mixture was stirred under N2 atmosphere at an external temperature of 110° C. for 2 h. The reaction mixture was allowed to warm up to room temperature, then diluted with DCM, and concentrated in the presence of silica gel. The resulting solid residue was purified by Combiflash™ chromatography (SiO2 (12 g), eluting with 1.5-25% EtOAc/hexanes) to afford the title compound as a foam.

Workup

temperatureto warm up to room temperature
concentrationconcentrated in the presence of silica gel
customThe resulting solid residue was purified by Combiflash™ chromatography (SiO2 (12 g), eluting with 1.5-25% EtOAc/hexanes)

Sources & evidence

ORD record: ord-d1c6a8e49d084bd1bab411ed097ae910
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383643B2

Reaction notes

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