N-bromobutanimide → (1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

HRID 1612108Notes

Reaction equation

HRID 1612108 reaction equation
[CH2:1]([C:3]1[C:4]([NH:11][C@@H:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][C@@H:13]2[OH:21])=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2].[Br:22]N1C(=O)CCC1=O>ClCCl>[Br:22][C:7]1[N:8]=[C:3]([CH2:1][CH3:2])[C:4]([NH:11][C@@H:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][C@@H:13]2[OH:21])=[N:5][C:6]=1[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58583341(1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 58583245(1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-olYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol (1.94 g, 6.8 mmol) in dichloromethane (35 mL) was purged with nitrogen and cooled to 0° C. This light purple/grey homogenous solution was treated with a single portion of N-bromosuccinimide (1.34 g, 7.5 mmol) instantly becoming a lighter color. The reaction was warmed to room temperature for 15 minutes, transferred to a separatory funnel, diluted with 100 mL additional dichloromethane, washed twice with water (75 mL), and once with brine (75 mL). The organics were dried over MgSO4, filtered, and concentrated to give a golden oil. This material was purified by biotage MPLC (90 g column, 15% ethyl acetate/heptane) to afford 2.24 g (90%) of the title compound as a pale yellow solid. IR (diffuse reflectance) 3416, 3355, 2969, 2941, 1555, 1538, 1482, 1385, 1378, 1295, 1285, 1200, 1181, 1043, 733 cm−1; OAMS supporting ions at: ESI+ 361.9; MS (EI) m/z 361 (M+); [α]25D=−35 (c 0.53, methylene chloride); Anal. Calcd for C17H20BrN3O: C, 56.36; H, 5.56; N, 11.60. Found: C, 56.46; H, 5.59; N, 11.50.

Workup

  1. temperatureThe reaction was warmed to room temperature for 15 minutes
  2. customtransferred to a separatory funnel
  3. washwashed twice with water (75 mL)
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a golden oil
  8. customThis material was purified by biotage MPLC (90 g column, 15% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-e5fa70c0a6ea45298035ca96938be40f
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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