Benzeneethanamine, alpha-methyl-, phosphate (1:1) → (S)-2'-(2-fluoropyridin-3-yl)-7'-(3-methylisoxazol-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 1970378Notes

Reaction equation

HRID 1970378 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:16]4[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=4)=[CH:9][CH:10]=3)[C@@:5]3([CH2:26][O:25][C:24]([NH2:27])=[N:23]3)[C:4]=2[CH:3]=1.[CH3:28][C:29]1[CH:33]=[C:32]([Sn](CCCC)(CCCC)CCCC)[O:31][N:30]=1.CC(N)CC1C=CC=CC=1.OP(O)(O)=O>>[F:22][C:17]1[C:16]([C:8]2[CH:9]=[CH:10][C:11]3[O:12][C:13]4[C:4](=[CH:3][C:2]([C:32]5[O:31][N:30]=[C:29]([CH3:28])[CH:33]=5)=[CH:15][CH:14]=4)[C@:5]4([CH2:26][O:25][C:24]([NH2:27])=[N:23]4)[C:6]=3[CH:7]=2)=[CH:21][CH:20]=[CH:19][N:18]=1

Participants

4

Reactant 3

HCID 62885Benzeneethanamine, alpha-methyl-, phosphate (1:1)HCID 27632553-Methyl-5-(tributylstannyl)isoxazoleHCID 67242922(S)-2'-bromo-7'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Product 1

HCID 45254129(S)-2'-(2-fluoropyridin-3-yl)-7'-(3-methylisoxazol-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Conditions

Temperature
100 °C

Procedure

A resealable was charged with (S)-2′-bromo-7′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (300 mg, 0.704 mmol), 3-methyl-5-(tributylstannyl)isoxazole (786 mg, 2.111 mmol), amphos (18.68 mg, 0.070 mmol) and argon purged dry dioxane (3 mL). The tube was purged with argon, sealed and heated with microwave at 100° C. for 1 h. The solution was concentrated. The crude product was purified via silica gel column chromatography (RediSep 12 g column) using 10-50% 90/10/1 DCM/MeOH/ammonia in DCM to afford (S)-2′-(2-fluoropyridin-3-yl)-7′-(3-methylisoxazol-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as a white solid. MS m/z=429.2 [M+H]+. Calcd for C24H17FN4O3: 428.42.

Workup

  1. custompurged dry dioxane (3 mL)
  2. customThe tube was purged with argon
  3. customsealed
  4. concentrationThe solution was concentrated
  5. customThe crude product was purified via silica gel column chromatography (RediSep 12 g column)

Sources & evidence

ORD record
ord-d4516384cb9743bc9b616304e12d5bb8
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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